Cu(Ⅰ)催化下2,3-二氢-1,4-苯并二噁烷类化合物的合成

doi:10.11944/j.issn.1000-0518.2016.02.150233

摘要/Abstract

摘要：

以CuBr为催化剂,1,4,7-三氮杂环壬烷衍生物为配体,K₂CO₃为碱,110 ℃下通过取代的邻碘代酚和取代的环氧化物的串联反应制备了2,3-二氢-1,4-苯并二噁烷类化合物。各种芳香取代的环氧化物和脂肪取代的环氧化物均能顺利的与邻碘代酚反应,产物收率64%~83%。讨论了底物取代基与产物收率的关系,推测了反应机理。并用NMR和元素分析确定了产物结构。

关键词: 二氢-苯并二噁烷, 邻碘代酚, 环氧化物, 三氮杂环壬烷衍生物

Abstract:

2,3-Dihydro-1,4-benzodioxins were prepared through a tandem reaction of epoxides and o-iodophenols catalyzed by CuBr/1,4,7-trisubstituted-1,4,7-triazonane with K₂CO₃ as the base at 110 ℃. All aryl and aliphatic epoxides reacted with o-iodophenols smoothly with yields of 64%~83%. The relationship between yields and substituent groups was described and the possible mechanism was discussed. The compounds were confirmed by NMR and element analysis.

Key words: dihydro-benzodioxin, o-iodophenol, epoxide, triazonane derivative

史兰香, 张宝华. Cu(Ⅰ)催化下2,3-二氢-1,4-苯并二噁烷类化合物的合成[J]. 应用化学, 2016, 33(2): 144-148.

SHI Lanxiang, ZHANG Baohua. Cu(Ⅰ)-Catalyzed Synthesis of 2,3-Dihydro-1,4-Benzodioxins[J]. Chinese Journal of Applied Chemistry, 2016, 33(2): 144-148.

[1]	史兰香, 张宝华. Cu(Ⅰ)催化下2,3-二氢-1,4-苯并二噁烷类化合物的合成[J]. 应用化学, 2016, 33(2): 0-0.
[2]	张万轩, 黄绵霞, 钟建华, 陈家威. 强碱性离子交换树脂支载的苯硒阴离子的制备及其反应性[J]. 应用化学, 1996, 0(3): 16-19.

Cu(Ⅰ)催化下2,3-二氢-1,4-苯并二噁烷类化合物的合成

Cu(Ⅰ)-Catalyzed Synthesis of 2,3-Dihydro-1,4-Benzodioxins

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